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Wikipedia

Butalbital

Butalbital is a barbiturate with an intermediate duration of action. Butalbital is often combined with other medications, such as paracetamol (acetaminophen) (as Butalbital/acetaminophen) or aspirin, for the treatment of pain and headache. The various formulations combined with codeine are FDA-approved for the treatment of tension headaches. Butalbital has the same chemical formula as talbutal but a different structure—one that presents as 5-allyl-5-isobutylbarbituric acid.[3]

Butalbital
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601009
Routes of
administration
By mouth
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Bioavailability20-45%
MetabolismLiver mainly CYP3A4
Elimination half-life35 hours [2]
ExcretionKidney
Identifiers
  • 5-(2-Methylpropyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
CAS Number
  • 77-26-9 Y
PubChem CID
  • 2481
IUPHAR/BPS
  • 7138
DrugBank
  • DB00241 Y
ChemSpider
  • 2387 Y
UNII
  • KHS0AZ4JVK
KEGG
  • D03182 Y
ChEBI
  • CHEBI:102524 Y
ChEMBL
  • ChEMBL454 Y
CompTox Dashboard (EPA)
  • DTXSID6022711
ECHA InfoCard100.000.926
Chemical and physical data
FormulaC11H16N2O3
Molar mass224.260 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C1NC(=O)NC(=O)C1(CC(C)C)C\C=C
  • InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16) Y
  • Key:UZVHFVZFNXBMQJ-UHFFFAOYSA-N Y
  (verify)

Preparations edit

Combinations include:

  • Butalbital/acetaminophen, Butalbital and acetaminophen (paracetamol), (trade names: Axocet, Bucet, Bupap, Cephadyn, Dolgic, Phrenilin, Forte, Sedapap)
  • Butalbital, paracetamol (acetaminophen), and caffeine (trade names: Fioricet, Esgic, Esgic-Plus, Orbivan, Fiormor, Fiortal, Fortabs, Laniroif)
  • Butalbital, paracetamol (acetaminophen), caffeine, and codeine phosphate (trade name: Fioricet#3 with Codeine)
  • Butalbital and aspirin (trade name: Axotal)
  • Butalbital, aspirin, caffeine (trade name: Fiorinal)
  • Butalbital, aspirin, caffeine, and codeine phosphate (trade name: Fiorinal#3 with Codeine)
  • Ergotamine tartrate, caffeine, butalbital, belladonna alkaloids (trade name: Cafergot-PB)

Contraindications edit

There are specific treatments which are appropriate for targeting migraines and headaches.[4] Butalbital is not recommended as a first-line treatment because it impairs alertness, brings risk of dependence and addiction, and increases the risk that episodic headaches will become chronic.[5] When other treatments are unavailable or ineffective, butalbital may be appropriate if the patient can be monitored to prevent the development of chronic headache.[5]

Side effects edit

Side effects for any psychoactive drug are difficult to predict, though butalbital is usually well tolerated. Commonly reported side effects for butalbital, some of which tend to subside with continued use, include:

Rare side-effects include Stevens–Johnson syndrome, an adverse reaction to barbiturates, and anaphylaxis.

The risk and severity of all side effects is greatly increased when butalbital (or butalbital-containing medications) are combined with other sedatives (ex. ethanol, opiates, benzodiazepines, antihistamines). In particular, butalbital, especially when combined with other sedatives (e.g. opioids), can cause life-threatening respiratory depression and death. Inhibitors of the hepatic enzyme CYP3A4 may also increase the risk, severity, and duration of side effects, many drugs inhibit this enzyme as do some foods such as grapefruit and the blood orange. Taking butalbital-based medications with some other drugs may also increase the side effects of the other medication.

Dangers and risks edit

Butalbital can cause dependence or addiction. Mixing with alcohol, benzodiazepines, and other CNS-depressants increases the risk of intoxication, increases respiratory depression, and increases liver toxicity when in combination with paracetamol (acetaminophen). Use of butalbital and alcohol, benzodiazepines, and other CNS-depressants can contribute to coma, and in extreme cases, fatality.

References edit

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Butalbital and Acetaminophen - FDA prescribing information, side effects and uses". drugs.com. from the original on 2018-01-21.
  3. ^ DE Patent 526854
  4. ^ American Academy of Neurology (February 2013), "Five Things Physicians and Patients Should Question", Choosing Wisely: an initiative of the ABIM Foundation, American Academy of Neurology, from the original on September 1, 2013, retrieved August 1, 2013, which cites
    • Silberstein SD (September 2000). "Practice parameter: evidence-based guidelines for migraine headache (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology". Neurology. 55 (6): 754–62. doi:10.1212/WNL.55.6.754. PMID 10993991.
    • Evers S, Afra J, Frese A, Goadsby PJ, Linde M, May A, Sándor PS (September 2009). "EFNS guideline on the drug treatment of migraine--revised report of an EFNS task force". European Journal of Neurology. 16 (9): 968–81. doi:10.1111/j.1468-1331.2009.02748.x. PMID 19708964. S2CID 9204782.
    • Institute for Clinical Systems Improvement (2011), , Institute for Clinical Systems Improvement, archived from the original on 2013-10-29, retrieved 2013-10-24
  5. ^ a b American Headache Society (September 2013), , Choosing Wisely: an initiative of the ABIM Foundation, American Headache Society, archived from the original on 3 December 2013, retrieved 10 December 2013, which cites
    • Bigal ME, Lipton RB (April 2009). "Excessive opioid use and the development of chronic migraine". Pain. 142 (3): 179–82. doi:10.1016/j.pain.2009.01.013. PMID 19232469. S2CID 27949021.
    • Bigal ME, Serrano D, Buse D, Scher A, Stewart WF, Lipton RB (September 2008). "Acute migraine medications and evolution from episodic to chronic migraine: a longitudinal population-based study". Headache. 48 (8): 1157–68. doi:10.1111/j.1526-4610.2008.01217.x. PMID 18808500. S2CID 17358333.
    • Scher AI, Stewart WF, Ricci JA, Lipton RB (November 2003). "Factors associated with the onset and remission of chronic daily headache in a population-based study". Pain. 106 (1–2): 81–9. doi:10.1016/S0304-3959(03)00293-8. PMID 14581114. S2CID 29000302.
    • Katsarava Z, Schneeweiss S, Kurth T, Kroener U, Fritsche G, Eikermann A, et al. (March 2004). "Incidence and predictors for chronicity of headache in patients with episodic migraine". Neurology. 62 (5): 788–90. doi:10.1212/01.WNL.0000113747.18760.D2. PMID 15007133. S2CID 20759425.

External links edit

  • Butalbital, Online Medical Dictionary
  • Butalbital and Acetaminophen (Systemic) (), MedicinePlus Drug Information
  • Controlled Substances in Schedule III, (), U.S. Drug Enforcement Administration

butalbital, barbiturate, with, intermediate, duration, action, often, combined, with, other, medications, such, paracetamol, acetaminophen, acetaminophen, aspirin, treatment, pain, headache, various, formulations, combined, with, codeine, approved, treatment, . Butalbital is a barbiturate with an intermediate duration of action Butalbital is often combined with other medications such as paracetamol acetaminophen as Butalbital acetaminophen or aspirin for the treatment of pain and headache The various formulations combined with codeine are FDA approved for the treatment of tension headaches Butalbital has the same chemical formula as talbutal but a different structure one that presents as 5 allyl 5 isobutylbarbituric acid 3 ButalbitalClinical dataAHFS Drugs comMicromedex Detailed Consumer InformationMedlinePlusa601009Routes ofadministrationBy mouthATC codenoneLegal statusLegal statusBR Class B1 Psychoactive drugs 1 CA Schedule IV DE Anlage II Authorized trade only not prescriptible UK Class B US Schedule III UN Psychotropic Schedule IIIPharmacokinetic dataBioavailability20 45 MetabolismLiver mainly CYP3A4Elimination half life35 hours 2 ExcretionKidneyIdentifiersIUPAC name 5 2 Methylpropyl 5 2 propenyl 2 4 6 1H 3H 5H pyrimidinetrioneCAS Number77 26 9 YPubChem CID2481IUPHAR BPS7138DrugBankDB00241 YChemSpider2387 YUNIIKHS0AZ4JVKKEGGD03182 YChEBICHEBI 102524 YChEMBLChEMBL454 YCompTox Dashboard EPA DTXSID6022711ECHA InfoCard100 000 926Chemical and physical dataFormulaC 11H 16N 2O 3Molar mass224 260 g mol 13D model JSmol Interactive imageSMILES O C1NC O NC O C1 CC C C C C CInChI InChI 1S C11H16N2O3 c1 4 5 11 6 7 2 3 8 14 12 10 16 13 9 11 15 h4 7H 1 5 6H2 2 3H3 H2 12 13 14 15 16 YKey UZVHFVZFNXBMQJ UHFFFAOYSA N Y verify Contents 1 Preparations 2 Contraindications 3 Side effects 4 Dangers and risks 5 References 6 External linksPreparations editCombinations include Butalbital acetaminophen Butalbital and acetaminophen paracetamol trade names Axocet Bucet Bupap Cephadyn Dolgic Phrenilin Forte Sedapap Butalbital paracetamol acetaminophen and caffeine trade names Fioricet Esgic Esgic Plus Orbivan Fiormor Fiortal Fortabs Laniroif Butalbital paracetamol acetaminophen caffeine and codeine phosphate trade name Fioricet 3 with Codeine Butalbital and aspirin trade name Axotal Butalbital aspirin caffeine trade name Fiorinal Butalbital aspirin caffeine and codeine phosphate trade name Fiorinal 3 with Codeine Ergotamine tartrate caffeine butalbital belladonna alkaloids trade name Cafergot PB Contraindications editThere are specific treatments which are appropriate for targeting migraines and headaches 4 Butalbital is not recommended as a first line treatment because it impairs alertness brings risk of dependence and addiction and increases the risk that episodic headaches will become chronic 5 When other treatments are unavailable or ineffective butalbital may be appropriate if the patient can be monitored to prevent the development of chronic headache 5 Side effects editSide effects for any psychoactive drug are difficult to predict though butalbital is usually well tolerated Commonly reported side effects for butalbital some of which tend to subside with continued use include Dizziness Respiratory depression impaired breathing Drowsiness Intoxicated feeling Light headedness Nausea Sedation Euphoria Severe impairment of judgment Diarrhea Memory Loss ConstipationRare side effects include Stevens Johnson syndrome an adverse reaction to barbiturates and anaphylaxis The risk and severity of all side effects is greatly increased when butalbital or butalbital containing medications are combined with other sedatives ex ethanol opiates benzodiazepines antihistamines In particular butalbital especially when combined with other sedatives e g opioids can cause life threatening respiratory depression and death Inhibitors of the hepatic enzyme CYP3A4 may also increase the risk severity and duration of side effects many drugs inhibit this enzyme as do some foods such as grapefruit and the blood orange Taking butalbital based medications with some other drugs may also increase the side effects of the other medication Dangers and risks editButalbital can cause dependence or addiction Mixing with alcohol benzodiazepines and other CNS depressants increases the risk of intoxication increases respiratory depression and increases liver toxicity when in combination with paracetamol acetaminophen Use of butalbital and alcohol benzodiazepines and other CNS depressants can contribute to coma and in extreme cases fatality References edit Anvisa 2023 03 31 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 784 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 2023 04 04 Archived from the original on 2023 08 03 Retrieved 2023 08 16 Butalbital and Acetaminophen FDA prescribing information side effects and uses drugs com Archived from the original on 2018 01 21 DE Patent 526854 American Academy of Neurology February 2013 Five Things Physicians and Patients Should Question Choosing Wisely an initiative of the ABIM Foundation American Academy of Neurology archived from the original on September 1 2013 retrieved August 1 2013 which cites Silberstein SD September 2000 Practice parameter evidence based guidelines for migraine headache an evidence based review report of the Quality Standards Subcommittee of the American Academy of Neurology Neurology 55 6 754 62 doi 10 1212 WNL 55 6 754 PMID 10993991 Evers S Afra J Frese A Goadsby PJ Linde M May A Sandor PS September 2009 EFNS guideline on the drug treatment of migraine revised report of an EFNS task force European Journal of Neurology 16 9 968 81 doi 10 1111 j 1468 1331 2009 02748 x PMID 19708964 S2CID 9204782 Institute for Clinical Systems Improvement 2011 Headache Diagnosis and Treatment of Institute for Clinical Systems Improvement archived from the original on 2013 10 29 retrieved 2013 10 24 a b American Headache Society September 2013 Five Things Physicians and Patients Should Question Choosing Wisely an initiative of the ABIM Foundation American Headache Society archived from the original on 3 December 2013 retrieved 10 December 2013 which cites Bigal ME Lipton RB April 2009 Excessive opioid use and the development of chronic migraine Pain 142 3 179 82 doi 10 1016 j pain 2009 01 013 PMID 19232469 S2CID 27949021 Bigal ME Serrano D Buse D Scher A Stewart WF Lipton RB September 2008 Acute migraine medications and evolution from episodic to chronic migraine a longitudinal population based study Headache 48 8 1157 68 doi 10 1111 j 1526 4610 2008 01217 x PMID 18808500 S2CID 17358333 Scher AI Stewart WF Ricci JA Lipton RB November 2003 Factors associated with the onset and remission of chronic daily headache in a population based study Pain 106 1 2 81 9 doi 10 1016 S0304 3959 03 00293 8 PMID 14581114 S2CID 29000302 Katsarava Z Schneeweiss S Kurth T Kroener U Fritsche G Eikermann A et al March 2004 Incidence and predictors for chronicity of headache in patients with episodic migraine Neurology 62 5 788 90 doi 10 1212 01 WNL 0000113747 18760 D2 PMID 15007133 S2CID 20759425 External links editButalbital Online Medical Dictionary Butalbital and Acetaminophen Systemic archive MedicinePlus Drug Information Controlled Substances in Schedule III archive U S Drug Enforcement Administration Retrieved from https en wikipedia org w index php title Butalbital amp oldid 1188722869 Preparations, wikipedia, wiki, book, books, library,

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